Efficient construction of the kedarcidin chromophore ansamacrolide

Org Lett. 2005 Jan 20;7(2):267-70. doi: 10.1021/ol0477374.

Abstract

[Structure: see text] The streamlined assembly of the ansamacrolide framework of the kedarcidin chromophore via an efficient atropselective Sonogashira coupling step is described. To this end, two newly improved practical syntheses of the cyclopentene and diyne fragments have been developed, which feature 0.2 mol % catalytic loadings for an RCM step and i-PrMgCl/CH2I2 as a new entry to gem-disubstituted epoxides from ketones, both being applicable to 49-g scales.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis
  • Alkenes / chemistry
  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Cyclization
  • Cycloparaffins / chemical synthesis*
  • Cycloparaffins / chemistry
  • Enediynes
  • Lactams, Macrocyclic / chemical synthesis*
  • Lactams, Macrocyclic / chemistry
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Molecular Structure
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / chemistry

Substances

  • Alkenes
  • Alkynes
  • Cycloparaffins
  • Enediynes
  • Lactams, Macrocyclic
  • Macrolides
  • Naphthalenes
  • kedarcidin chromophore